House holiday rentals in Safety Harbor

A charming Florida bungalow features a turquoise exterior with natural stone accents. The front porch is accessed by a concrete pathway lined with greenery, including tropical plants. A small entry door and window allow for natural light, framed by neatly placed shutters and landscaping.

4.92 out of 5 average rating, 284 reviews

Wonderful family friendly home in Dunedin FL

Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.

A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.

4.96 out of 5 average rating, 134 reviews

Heated saltwater pool|Spacious 4BR/3BA|

Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches. Happy holidays from our family to yours

Two modern tiny homes are situated next to each other, featuring a light color palette. Each unit has large glass doors leading to a spacious deck with railings, while lush greenery surrounds the area, providing a natural ambiance.

4.95 out of 5 average rating, 104 reviews

Surf Shack Tiny Home on Pinellas Trail w/ Heated P

Welcome to the Dunedin Tiny House Vacation Rentals! This Vacation Rental property offers daily, weekly or monthly rentals in 4 luxury tiny homes, a 3 bed bungalow & 1 bed cottage. The 6 Units along with a large Heated Pool are all tucked away within a thoughtfully planned, peaceful & wooded lot.... located right on the Pinellas Trail! The front entrance is conveniently located on Bayshore Blvd just north of the crossroad of Wilson. Once you enter the front door of your unit you will enjoy a

The exterior of a retro home is highlighted by a red vintage truck parked in the driveway. Lush greenery, including palm and flowering plants, surrounds the property, while two distinct pathways lead toward the entrance. The warm concrete driveway complements the inviting atmosphere.

5.0 out of 5 average rating, 119 reviews

Dream Retro, Pets Welcome-fenced, near beaches

Step into 1960, skip the ordinary vacation rental and stay somewhere your family will actually remember. From the colorful retro diner and vintage décor to the fenced backyard and playful details throughout the home, every room was designed to make you smile, walk to Publix. Just minutes from Clearwater Beach, you'll enjoy modern comforts wrapped in a one-of-a-kind nostalgic Florida experience. This is Not just a place to stay it’s an experience you’ll talk about long after your vacation ends.

A two-story beach-style house is depicted, featuring a covered porch with white railings and blue shutters on the windows. Potted plants adorn the porch, complementing the light exterior. Lush greenery is visible in the background, providing a tropical ambiance.

4.98 out of 5 average rating, 362 reviews

Steps to Downtown, Mins. to Waterfront | Sleeps 8

Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to gorgeous sunsets, shops, dining, breweries, and Pinellas Trail. Perfect for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this Dunedin favorite today !

4.88 out of 5 average rating, 125 reviews

Modern Paradise home near Clearwater Dunedin Beach

Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

A charming bungalow is depicted, featuring a light blue front door that invites guests in. The home is framed by a white picket fence, with a pebbled walkway leading to the entrance. Lush greenery and clear skies enhance the welcoming exterior.

4.98 out of 5 average rating, 114 reviews

Downtown Gem with Guest House - Walk to Main St!

Experience the best of Safety Harbor in a home designed for connection. Whether you’re planning a multi-generational reunion or a getaway with friends, the Blue Gecko offers the rare combination of togetherness and privacy. The Main House features 3 bedrooms and 2 baths with a chef-ready kitchen. Just steps across the yard, the Guest House provides a private retreat with its own queen bed, bath, and kitchen—perfect for grandparents or those in the group who appreciate a little extra quiet.

The exterior of a single-story house is presented, featuring a two-car garage and a well-maintained lawn. Lush green shrubs frame the entrance, and a small American flag is placed near the mailbox. A partly cloudy sky adds depth to the welcoming scene.

4.89 out of 5 average rating, 102 reviews

Nice Sparkling Clean Home with Pool.

Spacious family-friendly retreat. Three comfortable bedrooms and a cozy sitting room within the Master Bedroom, our home offers ample space for the entire family. With two full bathrooms, everyone can enjoy their own privacy and convenience. Step outside to the inviting pool area with a spacious enclosed patio. A Fully stocked kitchen is equipped with everything for preparing and enjoying delicious meals together. Plate settings for six to a comprehensive array of utensils and pots/pans.

A welcoming basket sits on a light-colored countertop, filled with snacks and bottled water. A decorative sign reads 'Welcome to Our Little Piece of Paradise.' A small potted plant is positioned nearby, and the kitchen's modern appliances are visible in the background.

4.98 out of 5 average rating, 106 reviews

Harbor Breeze Hideaway 4/2 King size bed!

Welcome to our beautiful city of Clearwater and to our unique Mid-Century modern style home. Centrally located within 20 minutes driving to the famous and award-winning Clearwater beach and 20 min driving to Tampa international airport. Easy access to local restaurants, bars, stores, super markets and mall. This comfortable home features unique design and layout with Mid-century modern furniture and decor, free Wi-Fi, smart TV’s, tile flooring; sleeps up to 10 people and has free parking.

4.94 out of 5 average rating, 116 reviews

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

5.0 out of 5 average rating, 48 reviews

Downtown Safety Harbor • Walk to Main St • Arcade•

Escape to our cozy 2-bedroom, 2-bath family hideaway in Safety Harbor, sleeping 5! Just a 3-block walk to Main Street's dining & shops. Enjoy a private backyard with a BBQ & fire pit, plus a fun-filled arcade game room. This bright, comfortable home is your perfect base for exploring Clearwater Beach, Tampa, Dunedin and the area’s many Gulf Coast attractions while staying in a quiet residential neighborhood. Features a fully equipped kitchen, dedicated workspace, and free parking.